Originally Posted by meunger11

If it were me, I'd take a quick positioning flight to JFK and take Emirates direct to Milan (MXP). Believe me, Mrs. Meunger11 of anybody loves to fly direct, but if you can sell the spousal unit on some bar action in the sky, and potentially first class: you can snag EK a380 first class for 85k/points pp OW and biz is 57.5k/pp OW. You can also shower. Did I mention EK tends to have a slew of seats in F and J on any given flight? I typically see 3-4 in F and 7 in J (I'd get a basic ExpertFlyer membership if you don't have one already). This is not unlike what JMN57 said about going via JFK to MXP.

Not sure how familiar you are with EK out of JFK, but you'd board straight from the lounge - fun little perk for a points F/J ticket.

Milan is beautiful and a ~3hr bullet train ride to Rome. (I'd recommend splurging for the Classe Executive on the Frecchiarossa - my wife and I love it). You'll see the gorgeous country-side on your way, or if you're feeling adventurous, you can hop on and off the regional and visit the pretty little towns along the way. Our friends did this for their 1yr anni and met us in Rome for brunch in The Vatican.

A 10yr anniversary seems worth splurging for on all accounts, including miles, but not what AA provides, which is usually 135k-180k J redemptions OW/pp direct to Europe. If you MUST fly American for whatever reason, look for Saver Awards, but do know they often only have one Saver per cabin. (Again, check Expert Flyer)